Problem is, while in class at present time, Theo is only bringing up the lesbian magazine no matter what day it is. I would think after the dialogue for it ends he should be bringing up what you are referencing here but he's not.
Developer needs to look into this as quests shouldn't be locked to a single one at a time.
In this case, I may possibly need to obtain 4,000 for Vol's 2 & 3 before I can proceed with Mabel's questline which is just plain dumb when they have nothing to do with one another other than Theo being involved with the both of them. 😡